Wilkinson played defense for with the USLPortland Timbers from 2001–2006, adding assistant coach duties in 2005 and 2006. Wilkinson retired as an active player and was named Head Coach and General Manager for Portland Timbers in September 2006. During the 2009 season, he directed the Timbers to the Commissioner's Cup as the regular season champion and a league record 24 game unbeaten string (14-0-10), smashing the previous record of 16.

Gavin not only played for Portland Timbers, but has also played for the New Zealand National Team 40 times in various competitions including World Cup Qualifiers and the Confederations Cup, playing against countries like the United States, Germany & Brazil.